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Given the complexity of the NBA's collective bargaining agreement, to execute a trade takes an artist. Understanding this, Bill Simmons has long referred to himself as the "Picasso of the Trade Machine" for his impressive ability to conceive sensible swaps. Well, I assume he's commenting on his proficiency and not on any particular stylistic leanings his works embody.
Picasso is regarded as one of the greatest painters in history, and Simmons has merely adopted that persona, much as Hassan Whiteside calls himself the Michael Jordan of Madden ‘11 and Charles Barkley refers to himself as the Joey Chestnut of the Little Debbie aisle.
But what if Pablo Picasso did work the Trade Machine? Or the other Masters of Western Civilization rose from their graves and took up an interest in armchair team-building? What could the Artists of the Trade Machine come up with?
PABLO PICASSO
Style: Cubism
Signature work: Guernica
Trade Machine Masterpiece: Carmelo Anthony to Knicks; Eddy Curry, Danilo Gallinari and Ronny Turiaf to Nuggets.
Picasso's Cubist movement sought to deconstruct subjects to their atomic elements and reassemble the pieces to provide new layers of perspective. What is ‘Melo at his core?
A great scorer (Danilo), occasionally in braids (Turiaf) and with a huge salary (Curry). Picasso was also prolific, so he'd follow up this trade with Turiaf for Fred Astaire and E-40, Curry for Michael Sweetney and Iceland's economy, and Gallinari for Allan Houston and Silvio Berlusconi.
EDOUARD MANET
Style: Impressionism
Signature work: The Luncheon on the Grass
Trade Machine Masterpiece: Al Jefferson to Jazz; Kosta Koufos and two picks to Wolves.
If Manet has an avatar in today's NBA, it would be the Timberwolves' David Kahn. Manet's Luncheon shocked society because of its utter destruction of all cloaks of mystery and its abrasive forthrightness. Nudes were hardly avant garde, but Manet's depiction of a bare woman picnicking with two dandies with brushstrokes evident and perspective all out of whack -- that broke all the rules. It was eroticism without decency.
In the NBA, when you make blatant cap-clearing moves, you're supposed to buy some cover by acquiring something tangible. When Joe Dumars shed the salaries of Chauncey Billups and Antonio McDyess in a cap dump, he at least took Allen Iverson(‘s expiring contract) back. When the Knicks bet the future on the Summer of ‘10, they sold a few tickets by getting the partially re-animated corpse of Tracy McGrady from Houston.
Kahn, with Al Jefferson? Nothing. Just Kosta Koufos and a couple of dice-roll draft picks. That cap dump was as naked as Manet's model, and more shocking.
VINCENT VAN GOGH
Style: Post-Impressionism
Signature work: Starry Night
Trade Machine Masterpiece: Kevin Garnett to Bobcats; Gilbert Arenas to Celtics; Gerald Wallace to Wizards.
Van Gogh's amazing oeuvre teems with a vivid palette and incredible emotional presence. As such, the league's most emotionally naked player, Garnett, heads to the franchise with the most striking palette, the Bobcats. I also suspect van Gogh would appreciate Gil's macabre sense of humor, and would understand that allowing KG and Stephen Jackson to bubble together in Charlotte would create a special brew of crazy.
Crash Wallace to D.C.? That just makes sense, even to an eccentric like van Gogh.
MARK ROTHKO
Style: Abstract Expressionism
Signature work: Untitled (1949)
Trade Machine Masterpiece: Paul Millsap to the Raptors; Jose Calderon and Reggie Evans to the Bobcats; Gerald Wallace to the Jazz.
Rothko was a virtuoso in the color field movement, dropping bougie jaws and spurring murmurs of "my dead iguana could paint that" at the same time. It's that marriage of the contextually complex and physically simple that has Rothko looking to move some stathead favorites around. Rothko was all about PER.
(And yes, great artists apparently love Gerald Wallace.)

from wikimedia.org
ANDY WARHOL
Style: Pop Art
Signature work: Campbell's Soup Cans (pictured above)
Trade Machine Masterpiece: LeBron James to Bobcats; Jordan Retro XIIIs collection to Heat.
Warhol's monuments to commerce defied the very definition of art, just as his trade suggestion defies the very rules of NBA deal-making. Nothing an ever-mystical "trade exception" can't fix. Warhol would argue that in the run-up to and aftermath of The Decision, LeBron became a commodity first and foremost; as such, being traded for an actual commodity cuts through at core honesty, which is what art is all about anyway.
GUSTAV KLIMT
Style: Symbolism
Signature work: The Kiss
Trade Machine Masterpiece: Greg Oden and Brent Barry (on a one-year Keith Van Horn special) to Spurs; George Hill to Blazers; Tony Parker to Rockets.
Klimt lived with his mother and two sisters into his 40s, but had some of the most erotic fine art of the 20th century. I feel like he'd be the kind of man who would appreciate Internet celebrity genitalia "art," as well as the Erin Barry saga. He might also write a paparazzi blog trying to peg Michael Redd and A.C. Green cheating on their spouses.
RENE MAGRITTE
Style: Surrealism
Signature work: The Treachery of Images
Trade Machine Masterpeice: Jay Williams to the Nets; Jayson Williams to the Magic; Jason Williams to the Bulls.
Ceci n'est pas une trade.
DESMOND MASON
Style: --
Signature work: A charcoal self-portrait
Trade Machine Masterpiece: Desmond Mason sign-and-trade to Clippers; Blake Griffin to L.A. Defenders of the D-League.
Stand down, young man. Recognize the eternal dunk champ.